The oldest woman you have had sex with

53
screenshot_20250225-182538-3-png.2526120
 
  • Like
Reactions: DaddyThick
When I was 18 (in 1978) I had sex many times with a married woman of 38. At the time, this seemed like a big age gap and was highly unusual (I thought). But now my 52 year old wife has a 28 year old lover, which doesn’t seem to be at all noteworthy to me. It’s funny how perceptions can change.
 
  • Like
Reactions: DeviantBiker
I was 20 and she was probably about 45, italian/american living in LA. The Summer of '88. She offered, she made the advance. But stupid, stupid me refused. Me and my damn Catholic morals.

To this day, now Im 57, I regret my bad decision. I will go to my grave repenting that I refused such an opportunity that rarely presents itself to a 20yr old. No matter that I have a hot hotwife who has given me 25 years of great pleasure. I regret that day I said no
 
hi guys mention the age of the oldest woman you have fucked...other than your wife......how was she in the bed....to start with i fucked a woman at her age if 57 and hot as hell....so craving for sex.......fucked her ass hole on her request......she is a friend of my MIL.
The oldest woman I have had sex with is 58, but that is not that old at all. However, your post made me think of the biggest age difference in terms of sex. I have just remembered a woman I had sex with when I was 23. She used to work as a cleaner in a medical centre where a friend of mine was working as a nurse. A couple of months after he starting working there, he arranged a birthday party and invited some of the staff members. She was about to turn 48 and she was divorced, but with a 14-year-old ....... My friend and many of the guests got a bit ...... but she was sober, because she had to drive back and pick up her ...... from her ex. We started to chat and had a good conversation. When she was about to leave, I asked for her phone number, but I did not call her. Around a week later, my friend told me she had been asking him about me and I told him that we had had a very good conversation. This led me to call her one day and she told me that she was off on a Thursday. I told her that we could meet after my university classes on that day and have lunch. She accepted. When we met, we had a good lunch and I could not take my eyes off her boobs. However, she seemed not to be interested in anything sexual. After lunch, I invited her to have a coffee and we went to a local café. I suddenly decided to ask her whether she would be interested in having sex with me. I did it writing the question on a small piece of paper. "Would you like to have sex with me. If so, just smile or laugh. Otherwise, return this piece of paper, so that I can use it somewhere else". She read it and started to laugh. I asked her: "Does it mean "yes?" And she said: "yes, why not... but we cannot go to my place today..."

We went to her car and I told her to go to a plantation area close to the sea, so we could hide. We had sex in her small car. I remember sucking her big boobs and how passionate she was while she was riding me. She loved it.

A couple of months late, I visited her one morning. She was wearing no underwear. It was a great fuck again but the condom broke and we did not have more condoms. I finished on her face.

Shortly after, she started a relationship with an older man, so we never had sex again.
 
The oldest woman I have had sex with is 58, but that is not that old at all. However, your post made me think of the biggest age difference in terms of sex. I have just remembered a woman I had sex with when I was 23. She used to work as a cleaner in a medical centre where a friend of mine was working as a nurse. A couple of months after he starting working there, he arranged a birthday party and invited some of the staff members. She was about to turn 48 and she was divorced, but with a 14-year-old ....... My friend and many of the guests got a bit ...... but she was sober, because she had to drive back and pick up her ...... from her ex. We started to chat and had a good conversation. When she was about to leave, I asked for her phone number, but I did not call her. Around a week later, my friend told me she had been asking him about me and I told him that we had had a very good conversation. This led me to call her one day and she told me that she was off on a Thursday. I told her that we could meet after my university classes on that day and have lunch. She accepted. When we met, we had a good lunch and I could not take my eyes off her boobs. However, she seemed not to be interested in anything sexual. After lunch, I invited her to have a coffee and we went to a local café. I suddenly decided to ask her whether she would be interested in having sex with me. I did it writing the question on a small piece of paper. "Would you like to have sex with me. If so, just smile or laugh. Otherwise, return this piece of paper, so that I can use it somewhere else". She read it and started to laugh. I asked her: "Does it mean "yes?" And she said: "yes, why not... but we cannot go to my place today..."

We went to her car and I told her to go to a plantation area close to the sea, so we could hide. We had sex in her small car. I remember sucking her big boobs and how passionate she was while she was riding me. She loved it.

A couple of months late, I visited her one morning. She was wearing no underwear. It was a great fuck again but the condom broke and we did not have more condoms. I finished on her face.

Shortly after, she started a relationship with an older man, so we never had sex again.
Wow 🥵